Just two hours northwest of Santiago is the port city of Valparaiso. It was built on dozens of hills right at the ocean's edge and is basically a cartographer's worst nightmare. The streets curve up the hills like snakes, and everywhere you turn there are narrow, graffiti-adorned stairways that wander off... somewhere. There's really no such thing as a direct route in Valparaiso, just lots of urban adventures.
The city is full of color, with brightly painted buildings, crumbling Spanish architecture and gorgeous street art on every surface imaginable. We stayed at the Casa Valparaiso Hostel, which is located on one of the central hills, Cerro Concepcion. The hostel was cheap (about $20 a night for a private room) and in a good location. It's pretty noisy on the weekend though, so either bring your earplugs or join the party.
We spent most of Saturday just wandering around the city eating good food and exploring the hills. At night we went in search of ice cream and discovered a pride parade. Naturally we joined the crowd following the floats and had a fantastic time dancing in the streets and watching the drag shows. Since Chile still has a lot of problems with homophobia, it was an especially amazing experience to celebrate pride here.
The next day we went to check out La Sebastiana, one of Pablo Neruda's three houses. Neruda is one of Chile's most famous writers, best known for his romantic and political poetry, and was also very active in politics during his time. His house was really interesting, made up of five stories with a nautical theme and unique architecture. It's full of his collections and is a great way to learn about one of the most famous figures in recent Chilean history.
Valparaiso is a great weekend escape from Santiago. With all its little alleys and narrow streets, there's always something new to discover. We'll definitely be back again very soon!